Chemistry 3719 - Organic Chemistry I

Professor : Dr. Peter NorrisOffice : 6014 Ward BeecherTelephone : (330) 941-1553Email : pnorris@ysu.eduWebsites :

http://www.as.ysu.edu/~pnorris/public_html

www.chemfinder.com

Lecture needs:

• Carey

• Molecular models

• Adobe Acrobat Reader

• Web access

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Molecular Models – www.darlingmodels.com

May be used on exams, will be used in lectureYSUYSU

Lab needs:

• Pavia, Lampman, Krizand Engel

• Goggles

• Lab coat

• Bound notebook

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Chemistry 3719 and 3720 (and labs)

Lectures

• Structure and nomenclature of compounds and groups

• Physical properties and analysis of materials

• Reactivity and transformations with reagents

• Importance of organic compounds in other subjects

Labs

• Glassware and equipment used to prepare organics

• Instrumentation used to analyze compounds

• Keeping a good notebook of lab preparations

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Chemistry 3719R and 3720R (Recitation)

Objectives

• Practice the problems sets, old exams

• Practice the problems from the book

• Ask ?? of a professional chemist (other than lecture Prof)

• To encourage students to keep up with material (quizzes)

When: 12-12.50 or 1-1.50 on Mondays

(1 Semester hour, Separate grade to 3719/3719L)

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Chemistry 3719 Personnel

Dr. Peter Norris3719 lecture

Dr. John Jackson3719 recitation

Calvin Austin3719 lab

Lucas Beagle3719 lab

Lemuel Carlisle3719 lab

Brian Dobosh3719 lab

Mike Evans3719 lab

Ashley Malich3719 lab

Kevin White3719 lab

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Some does and don'ts for 3719 and 3720

Does• Prepare for lecture and lab; read ahead

• Ask questions at any time; lecture, recitation, office hours

• Use all of your resources; email, website, tutors

• If you struggled in General Chemistry, seek help soon

Don'ts• Don’t get behind, blow off class, ignore the available help

• Don’t wait until October to say “dude, I thought I knew the stuff.”

• Don’t complain when you get 20/100 if you ignore the above

Get help : pnorris@ysu.eduYSUYSU

Peter Norris B.Sc., Ph.D.

Born : 1965, Liverpool, England

B.Sc. Chemistry : 1986, Salford University, England

Ph.D. Organic Chemistry: 1992, The Ohio State University

Post-doctoral : 1993-96, American University, Wash’n DC

Assistant Professor : 1996-2000 YSU Chemistry

Associate Professor : 2000-2004 YSU Chemistry

Full Professor : 2004 – present YSU Chemistry

40 publications, graduated 23 Masters degree students since 1998

~ $1,000,000 in grant money since 1999

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"Cu(I)-Catalyzed formation of D-mannofuranosyl 1,4-disubstituted 1,2,3-triazole carbohybrids," P.L. Miner, T.R. Wagner, and P. Norris, Heterocycles 2005, 65, 1035-1049.

>40 total, most with YSU undergrad or MS students as coauthors

"Crystal structure of 1-(2,3:5,6-di-O-isopropylidene-beta-D-mannofuranosyl)-1H-[1,2,3]triazol-4,5-dicarboxylic acid diethyl ester," H. Seibel, P.L. Miner, P. Norris, and T.R. Wagner, J. Chem. Cryst., 2006.

"Application of Bis(diphenylphosphino)ethane in Staudinger-type N-Glycosyl Amide Synthesis," D. P. Temelkoff, C. R. Smith, D. A. Kibler, S. McKee, S. Duncan, M. Zeller, M. Hunsen, and P. Norris, Carbohydrate Research, 2006, 341, 1645-1656.

"N-Glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide," D. P. Temelkoff, M. Zeller, and P. Norris, Carbohydrate Research 2006, 341, 1081-1090.

Research and Publication

"Crystal and molecular structure of 6,7-dideoxy-1,2;3,4;9,10-tris-O-(1-methylethylidene)-D-erythro-alpha-D-galacto-undecopyranosid-8-ulose," T. D. Weaver, M. Zeller, and P. Norris, J. Chem. Cryst., 2006.

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What is Organic Chemistry?

The study of the compounds that contain carbon and the reactions of those materials (millions known)

Why a whole year of Organic?

Carbon can bond in multiple ways to form a huge number of different molecules, and these compounds form the basis of many different disciplines, e.g.:

Biology (DNA, proteins, carbohydrates)

Medicine and Pharmacy (Aspirin, Taxol, AZT)

Chemical Engineering (oil, plastics, fine chemicals)

Forensics (Biological materials, chemical tests)

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From Organic Chemistry to Biology, Medicine, Pharmacy, etc.From Organic Chemistry to Biology, Medicine, Pharmacy, etc.

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N-acetylneuraminic acid

Tamiflu - Giliad/Roche

Relenza - GSK

From Scientific American – www.sciam.com

CO2EtO

NH3.HPO4

AcHN

O CO2H

H2N NH

AcHN

OHOH

OH

O CO2H

AcHN

OHOH

OH

OH

VancomycinYSUYSU

Staphylococcus Staphylococcus aureusaureus –– Norris/FaganNorris/Fagan

Gram-positive, cluster-forming coccus, causes food poisoning, endocarditis, osteomyelitis, septiceamia, infections on implants

Organic Chemistry – Materials and Uses

Organic Chemistry

chemicalsynthesis

NewCompounds

NewMedicines

medicinal

chemistry

materials

chemistryNew

Materials

Pharmacy,Medicine

Nanotech,Engineering

Biochemistryand

Chemical Biology

Proteomics,Genetics

~1800 – Organic Chemistry : the chemistry of natural products based on carbon

2006 – Organic Chemistry : “molecular engineering”

Chemistry 3719Chemistry 3719--37203720

H

CH

HH

Timeline1807 Berzelius introduces the term “Organic Chemistry” to describe

the study of compounds isolated from nature

1828 Wöhler makes urea, the first natural organic compound to be

synthesized in the laboratory

1890 Fischer studies the chemistry of proteins, carbohydrates and

the nucleic acids - Biochemistry

1950 Woodward and Eschenmoser complete the first total synthesis

of Vitamin B12. NMR begins to be useful.

1990 Kishi, Nicolau, Smith, Schreiber, etc. complete total syntheses

of compounds such as Brevetoxin B, Taxol, etc.

2000 Chemical Biology, Molecular Engineering

OHcatalytic H+

+OH

O

O

O

OH

OH

OH

OH

HO HO OH

OH

HO O

O

HHH+

transfer

OH

O

O

OH

H2O

OH

O

(- H2O)

(- H2O)

(- H+)

Teaching Philosophy: Organic Chemistry as a Language

H2N

O

NH2

UREA - 1828

Natural Products Chemistry

Ley, Veitch, Beckmann, Burke, Boyer and Maslen. ACIEE, August 2007

Carey Chapter 1 - Chemical Bonding

“Structure determines properties”

• Atomic and electronic structure of atoms

• Ionic and covalent bonding

• Electronegativity and polar covalent bonds

• Structures of organic compounds - representations

• Resonance within molecules

• Shapes of molecules

• Molecular orbitals and orbital hybridization

Periodic Table of the Elements

1.1 Atoms, electrons, and orbitals

Probability distribution for an electronFigure 1.1

Boundary surfaces of a 1s and 2s orbitalFigure 1.2

Boundary surfaces of the 2p orbitalsFigure 1.3

Electronic Configurations of Atoms

Electronic Structure of Atoms

Atom Atomic No. Electronic Structure

H 1 1s1

He 2 1s2

Li 3 1s2 2s1

Be 4 1s2 2s2

B 5 1s2 2s2 2px1

C 6 1s2 2s2 2px1 2py1

N 7 1s2 2s2 2px1 2py1 2pz1

O 8 1s2 2s2 2px2 2py1 2pz1

1.1 General Concepts

• Orbitals higher in energy further they are from nucleus.

• Designated by principal quantum number (1, 2, 3, etc.).

• Degenerate orbitals (same energy) fill up singly before they double up (Aufbau).

• Maximum of two electrons per orbital, each having opposite spin (Pauli exclusion principle).

• Impossible to know both the speed and location of an electron at the same time (Heisenberg uncertainty).